(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane
• CAS No.: 93379-49-8
• Molecular Formula: C₃₁H₃₀O₄
• Molecular Weight: 466.577
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID701317964
• Nikkaji Number: J231.888A
• Mol file: 93379-49-8.mol

Synonyms:93379-49-8;(+)-Taddol;((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol);(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane;(S,s)-taddol;[(4S,5S)-5-[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-diphenylmethanol;C31H30O4;(4S,5S)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetraphenyldioxolane-4,5-dimethanol;MFCD00010079;[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethanol);(S)-Taddol;(+)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-D-threitol;(4S,5S)-Taddol;SCHEMBL4383952;DTXSID701317964;AKOS016842871;AM62783;CS-W013767;SC11819;AS-11054;B2048;T71474;A844577;A1-24353;1,1,4,4-Tetraphenyl-2-O,3-O-isopropylidene-D-threitol;(+)-45-Bis[hydroxy(diphenyl)methyl]-22-dimethyl-13-dioxolane;((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis-(diphenylmethanol);(2S,3S)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol;(4S,5S)-4,5-Bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane;(+)-trans-Alpha,alpha'-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol);(4S,5S)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetraphenyldioxolane-4,5-dimethanol, 97%;(4S,5S)-2,2-Dimethyl- alpha , alpha , alpha ', alpha '-tetraphenyldioxolane-4,5-dimethanol;[(4R,5R)-5-(HYDROXY-DIPHENYL-METHYL)-2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL]-DIPHENYL-METHANOL;1,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-.alpha.,.alpha.,.alpha.',.alpha.'-tetraphenyl-, (4S,5S)-;1,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-alpha4,alpha4,alpha5,alpha5-tetraphenyl-, (4S,5S)-

Chemical Property of (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 193-196 °C(lit.)
• Refractive Index: 1.615
• Boiling Point: 633.2 °C at 760 mmHg
• PKA: 12.28±0.29(Predicted)
• Flash Point: 336.7 °C
• PSA: 58.92000
• Density: 1.2 g/cm³
• LogP: 5.37870
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 466.21440943
• Heavy Atom Count: 35
• Complexity: 574

Purity/Quality:

99% ^*data from raw suppliers

(+)-TADDOL ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O)C
• Isomeric SMILES: CC1(O[C@@H]([C@H](O1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O)C
• Uses: Ligand for enantioselective Lewis-acid mediated Diels-Alder, allyltitanation of aldehydes, and Michael-Mukaiyama additions promoted by chiral Ti-complexes.

Technology Process of (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane

There total 5 articles about (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (73346-73-3) + phenylmagnesium bromide → (S,S)-taddol (93222-42-5,93379-48-7,93379-49-8,118139-82-5,126639-52-9,37031-30-4)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)80147-1

Reference yield:

bromobenzene (108-86-1,52753-63-6) + (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (73346-73-3) → (S,S)-taddol (93222-42-5,93379-48-7,93379-49-8,118139-82-5,126639-52-9,37031-30-4)

Guidance literature:

With iodine; magnesium; In tetrahydrofuran; Reflux;

DOI:10.1021/jacs.7b09947

Reference yield:

bromobenzene (108-86-1,52753-63-6) + ethyl (4R,5R)-5-benzoyl-2,2-dimethyl-1,3-dioxolane-4-carboxylate → (R,R)-TADDOL (93379-48-7) + (S,S)-taddol (93222-42-5,93379-48-7,93379-49-8,118139-82-5,126639-52-9,37031-30-4)

Guidance literature:

bromobenzene; With magnesium; In tetrahydrofuran;

ethyl (4R,5R)-5-benzoyl-2,2-dimethyl-1,3-dioxolane-4-carboxylate; In tetrahydrofuran; at -20 - 20 ℃; for 24.5h; Overall yield = 43 %; Overall yield = 200.3 mg;

DOI:10.1002/ejoc.201701695

upstream raw materials:

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

bromobenzene

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate

Downstream raw materials:

[(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,4-dimethyl-1H-pyridin-2-one

[(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4-methoxy-1-methyl-1H-pyridin-2-one

[(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4a-ethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Refernces

• 1、 Zhang, Zhao-Fei,Yang, Xiao-Chao,Lu, Hui-Jie,Wang, Min-Can. "Enantioselective Direct Synthesis of syn- and anti-α,β-Dihydroxy γ-Keto Esters Using a Dinuclear Zinc–AzePhenol Complex". . p. 785 - 793. Retrieved 2018/02/21.
• 2、 Allmendinger, Simon,Kinuta, Hirotaka,Breit, Bernhard. "Easily accessible TADDOL-derived bisphosphonite ligands: Synthesis and application in the asymmetric hydroformylation of vinylarenes". supporting information. p. 41 - 45. Retrieved 2015/03/03.